The Wealthy Entrepreneur
Why Only 33% of Family Businesses Survive: The Succession Conversation with Bobby Mascia
February 10, 2026
Here’s a shocking insight: most entrepreneurs build unsellable businesses. And, only 33% of family businesses actually survive. So, what’s the secret? Mastering succession planning, it would turn out.
In this episode of The Wealthy Entrepreneur, host Bob Gauvreau and Bobby Mascia, Founder of Green Ridge Wealth Planning and Family Office operator, explore how to architect a business for both profitability and transferability, why family succession fails 67% of the time and the counter-intuitive tax strategy that turns reinvestment into long-term wealth. 


From the operational structures that separate founders from their businesses to mastering the art of succession planning, this episode is a masterclass in learning how to stay profitable, cut through the noise and avoid getting trapped by your own operations. 


If you have something to say about being a wealthy entrepreneur and want to join the conversation, let us know here: https://www.wealthyentrepreneur.co/the-wealthy-entrepreneur-podcast-guest-submission. Look forward to having you on the podcast!


About Bobby:
Bobby Mascia is a Registered Investment Advisor and Founder of Green Ridge Wealth Planning, specializing in comprehensive wealth strategies for business owners and entrepreneurs. With a background spanning family business operations (scaling Dunkin' Donuts and Baskin-Robbins franchises from 20 to 40 locations) and financial advisory, he has built a fiduciary practice focused on bridging the gap between business performance and personal wealth. He’s taken his expertise to the page through the book, “Unchained”, a business memoir exploring the trials, failures and breakthroughs of entrepreneurial life, and hosts the “Business Unchained” podcast, as well. His work centers on making businesses "exit-ready", positioning owners for sustainable growth, reduced operational friction, and strategic optionality, with an ambitious goal to help 1,000 business owners achieve exit readiness by 2036. 


Connect with Bobby: 
Website: https://bobbymascia.com/ 
LinkedIn: https://www.linkedin.com/in/rmascia/ 
Instagram: https://www.instagram.com/bobbymascia/?hl=en 
Green Ridge Wealth Planning Website: https://grwealthplan.com/ 
Bobby’s Book: https://www.amazon.in/Unchained-Entrepreneurship-Family-Business-Balance-ebook/dp/B0GCB1C51T 
Bobby’s Podcast: https://www.youtube.com/@bobbymascia 


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Let’s continue to work on becoming a Wealthy Entrepreneur!



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